CN105623198B - A kind of highly thermal-conductive resin composition and its application - Google Patents
A kind of highly thermal-conductive resin composition and its application Download PDFInfo
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L63/10—Epoxy resins modified by unsaturated compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Abstract
The invention discloses a kind of highly thermal-conductive resin composition, by weight including following component：Bi-maleimide modified 40 75 parts of epoxy resin, flexible 5 40 parts of modified epoxy, 360 480 parts of heat filling, 8 30 parts of curing agent, 26 parts of coupling agent, 0.05 0.85 parts of curing accelerator, 15 parts of additive.Highly thermal-conductive resin composition of the present invention, by introducing the advantages of bi-maleimide modified epoxy resin combines epoxy resin and BMI in system, toughening modifying resin and heat filling are added simultaneously, makes new resin combination that there is excellent toughness, heat conductivility and higher Tg.The metal-based copper-clad plate prepared using the resin combination of the present invention, there is high thermal conductivity factor, breakdown voltage height, peel strength is high, Tg is higher and the Good All-around Properties such as pliability is good.
Description
Technical field
The invention belongs to technical field of electronic materials, and in particular to a kind of highly thermal-conductive resin composition, invention additionally discloses
The metal-based copper-clad plate made using above-mentioned highly thermal-conductive resin composition.
Background technology
In copper-clad laminate field, in general, highly heat-conductive material is from the good epoxy resin of cohesive as base
Body, epoxyn are a kind of widely used adhesive, and its adhesiveness is good, and cohesive strength is high, and it is excellent that compatibility is good etc.
Point.But deficiency is shown slightly in terms of heat resistance and electrical property.And bimaleimide resin monomer reactivity is high, during polymerization without point
Son discharges, and polyimides (PI) of the generation with high-fire resistance after curing reaction, end properties are stable, can be in wide temperature range
It is interior to keep higher physical and mechanical properties, and electrical property is very excellent, have high Tg, good stability of the dimension, volume resistance big etc.
Advantage.But toughness of products is poor after solidifying, caking property deficiency.Lead to more aromatic diamine modifications, epoxy resin modification, pi-allyl at present
Compound modified, modified rubber, it is cyanate modified, polyphenyl ether modified, thermoplastic resin modified the methods of to improve span carry out acyl
The toughness and caking property of imide resin.
Bimaleimide resin is in copper-clad plate field, the application of allyl monomer modified bismaleimide compound
It is constantly subjected to pay close attention to and studies.Wherein, (the applying date of Application No. 200910189544.6：2009.11.24 publication number：
101735611, publication date：2011.6.16 height is added in the BMI resin systems that Chinese patent) is modified by allyl phenol to lead
Manufactured copper-clad plate after the filler of heat, has excellent heat resistance and electrical property, but less than 1.0W/ in terms of thermal conductivity
More than mK, even if removing reinforcing material thermal conductivity also less than 1.5W/mK.If further improve thermal conductivity by increasing filler
To more than 1.8W/mK, then occur that breakdown voltage substantially reduces.
In the BMI resin systems that another allyl phenol is modified, although can be by pliability resin, such as nitrile rubber, phenol oxygen
The flexible material of the macromolecules such as resin further improves the toughness of solidfied material, still, because nitrile rubber, phenoxy resin
Molecular weight is big, and " island " structure is formed in curing system, the interfacial bonding property of resin and heat filling is reduced, is Metal Substrate
The electrical property of copper-clad plate is brought under defect, particularly high temperature, super-humid conditions, and breakdown voltage quickly reduces.
The content of the invention
It is an object of the invention to provide a kind of highly thermal-conductive resin composition, has excellent high-termal conductivity, and good is electrical
Energy, heat resistance, pliability and cohesive, and processing characteristics, it is possible to provide by its making High thermal conductivity cellophane good pliability,
Meet high heat conduction demand.
It is a further object to provide a kind of Metal Substrate made using above-mentioned highly thermal-conductive resin composition to cover copper
Plate, it has the performance such as high-termal conductivity, high-breakdown-voltage, higher glass transition temperature and excellent heat resistance.
The technical solution adopted in the present invention is a kind of highly thermal-conductive resin composition, by weight including following component：It is double
Maleimide-modified epoxy resin 40-75 parts, flexible modified epoxy 5-40 parts, heat filling 360-480 parts, curing agent
8-30 parts, coupling agent 2-6 parts, curing accelerator 0.05-0.85 parts, additive 1-5 parts.
The features of the present invention also resides in,
Bi-maleimide modified epoxy resin be N- to the Maleimide-modified epoxy resin of carboxyl phenyl, diamine with
Bismaleimide compound modified epoxy or dihydric phenol and bismaleimide compound modified epoxy are any one
Kind or at least two mixing；
N- is N- to the Maleimide-modified epoxy resin of carboxyl phenyl to carboxyl phenyl maleimide and epoxy resin
Reaction is made；
Diamine and bismaleimide compound modified epoxy are diamine, BMI and asphalt mixtures modified by epoxy resin
Fat ternary polymerization reaction gained, wherein diamine are MDA, diaminodiphenylsulfone, double (the 3- aminobenzene oxygen of 1,3-
Base) double (3- amino-benzene oxygens) phenylbenzenes of benzene or 4,4-；
Dihydric phenol and bismaleimide compound modified epoxy be dihydric phenol, bismaleimide compound and
Epoxy resin ternary polymerization reaction gained, wherein dihydric phenol are that diallyl bisphenol, diallyl Bisphenol F or diallyl are double
Phenol S.
Epoxy resin used in above-mentioned modification be bisphenol A epoxide resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin,
Biphenyl type epoxy resin, alicyclic based epoxy resin, epoxy resins of phenol formaldehyde type, Study On O-cresol Epoxy Resin, bisphenol-A phenol
Formaldehyde epoxy resin, dicyclopentadiene type novolac epoxy resin, aralkylphenol type epoxy resin, the multi-functional epoxy tree of class containing naphthalene nucleus
In fat or anthracycline-containing polyfunctional epoxy resin any one or at least two mixing；Bismaleimide compound is point
Compound containing two or more maleimide base group in minor structure, it is diphenyl methane dimaleimide, diphenyl ether pair
Maleimide or diphenyl sulphone (DPS) BMI.
The epoxy resin of flexible modification is modifying epoxy resin by organosilicon, acrylonitrile butadiene rubber modified epoxy resin, dimeric dibasic acid change
In property epoxy resin or soybean oil modified epoxy resin any one or at least two combination.
Curing agent is phenol Linear phenolic resin, ortho-cresol novolac resin, bisphenol A phenolic resin, dicyclopentadiene type
Phenolic resin, phenolic resin containing naphthalene nucleus, aralkylphenol type phenolic resin, two amine type benzoxazines, bisphenol A-type benzoxazine,
In bisphenol-f type benzoxazine or modified by cardanol benzoxazine any one or at least two combination.
Heat filling be breaking type aluminum oxide of the electrical conductivity below 50 μ s/cm, spherical type aluminum oxide, alumina whisker,
In aluminium nitride, boron nitride, magnesia or carborundum any one or at least two mixing.
Curing accelerator is glyoxaline compound, wherein, glyoxaline compound is 2-methylimidazole, the methyl miaow of 2- ethyls -4
Azoles, 2- phenylimidazoles, 2- undecyl imidazoles, 1 benzyl 2 methyl imidazole, 2- heptadecyl imidazoles, 2 isopropyl imidazole, 2-
Any one in phenyl -4-methylimidazole, 2- dodecyl imidazoles or 1- 1-cyanoethyl-2-methylimidazoles or at least two
Mixture.
Coupling agent is amino silicane coupling agent, epoxy silane coupling, isocyanates silane coupler or titanate esters
In class coupling agent any one or at least two mixture；Additive is appointing in dispersant, defoamer or levelling agent
Anticipate a kind of or at least two mixing, wherein, dispersant be modified polyurethane or acidic polyester with unsaturated polyamide and salt
Birds of the same feather flock together compound；Defoamer is modified alkanone, modified polyorganosiloxane or silicon modified organic polymer；Levelling agent is polysiloxanes or third
Olefin(e) acid ester copolymer.
The highly thermal-conductive resin composition also includes solvent, and solvent is acetone, butanone, methanol, alcohol, toluene, dimethylbenzene, N,
Any one in dinethylformamide, glycol monoethyl ether, propylene glycol monomethyl ether, ethyl acetate or cyclohexanone or at least two
Mixing.
Another technical scheme of the present invention is a kind of high heat conduction metal-based copper-clad plate, including metal substrate and
Above-mentioned highly thermal-conductive resin composition coated in metallic substrate surfaces；Described metal substrate be aluminium sheet, aluminium alloy plate, iron plate,
Ferroalloy plate or copper coin.
The invention has the advantages that combine epoxy by introducing bi-maleimide modified epoxy resin in system
Resin and the advantages of BMI, while add toughening modifying resin and heat filling, there is new resin combination excellent tough
Property, heat conductivility and higher Tg.The metal-based copper-clad plate prepared using the resin combination of the present invention, has thermal conductivity factor
High (>=1.8W/m.k), breakdown voltage high (>=6.0kV), peel strength high (>=1.05N/mm), Tg higher (>=135 DEG C) and
Pliability waits well Good All-around Property.
Embodiment
With reference to embodiment, the present invention is described in detail.
A kind of highly thermal-conductive resin composition of the present invention, by weight including following component：Bi-maleimide modified epoxy
Resin 40-75 parts, flexible modified epoxy 5-40 parts, heat filling 360-480 parts, curing agent 8-30 parts, coupling agent 2-6
Part, curing accelerator 0.05-0.85 parts, additive 1-5 parts.
Bi-maleimide modified epoxy resin be N- to the Maleimide-modified epoxy resin of carboxyl phenyl, diamine with
Bismaleimide compound modified epoxy or dihydric phenol and bismaleimide compound modified epoxy are any one
Kind or at least two mixing；
N- is N- to the Maleimide-modified epoxy resin of carboxyl phenyl to carboxyl phenyl maleimide and epoxy resin
Reaction is made；
Diamine and bismaleimide compound modified epoxy are diamine, BMI and asphalt mixtures modified by epoxy resin
Fat ternary polymerization reaction gained, wherein diamine are MDA, diaminodiphenylsulfone, double (the 3- aminobenzene oxygen of 1,3-
Base) double (3- amino-benzene oxygens) phenylbenzenes of benzene or 4,4-；
Dihydric phenol and bismaleimide compound modified epoxy be dihydric phenol, bismaleimide compound and
Epoxy resin ternary polymerization reaction gained, wherein dihydric phenol are that diallyl bisphenol, diallyl Bisphenol F or diallyl are double
Phenol S.
Epoxy resin used in above-mentioned modification be bisphenol A epoxide resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin,
Biphenyl type epoxy resin, alicyclic based epoxy resin, epoxy resins of phenol formaldehyde type, Study On O-cresol Epoxy Resin, bisphenol-A phenol
Formaldehyde epoxy resin, dicyclopentadiene type novolac epoxy resin, aralkylphenol type epoxy resin, the multi-functional epoxy tree of class containing naphthalene nucleus
In fat or anthracycline-containing polyfunctional epoxy resin any one or at least two mixing；Bismaleimide compound is point
Compound containing two or more maleimide base group in minor structure, it is diphenyl methane dimaleimide, diphenyl ether pair
Maleimide or diphenyl sulphone (DPS) BMI.
The epoxy resin of flexible modification is modifying epoxy resin by organosilicon, acrylonitrile butadiene rubber modified epoxy resin, dimeric dibasic acid change
In property epoxy resin or soybean oil modified epoxy resin any one or at least two combination.
Curing agent is phenol Linear phenolic resin, ortho-cresol novolac resin, bisphenol A phenolic resin, dicyclopentadiene type
Phenolic resin, phenolic resin containing naphthalene nucleus, aralkylphenol type phenolic resin, two amine type benzoxazines, bisphenol A-type benzoxazine,
In bisphenol-f type benzoxazine or modified by cardanol benzoxazine any one or at least two combination.
Heat filling be breaking type aluminum oxide of the electrical conductivity below 50 μ s/cm, spherical type aluminum oxide, alumina whisker,
In aluminium nitride, boron nitride, magnesia or carborundum any one or at least two mixing.
Curing accelerator is glyoxaline compound, wherein, glyoxaline compound is 2-methylimidazole, the methyl miaow of 2- ethyls -4
Azoles, 2- phenylimidazoles, 2- undecyl imidazoles, 1 benzyl 2 methyl imidazole, 2- heptadecyl imidazoles, 2 isopropyl imidazole, 2-
Any one in phenyl -4-methylimidazole, 2- dodecyl imidazoles or 1- 1-cyanoethyl-2-methylimidazoles or at least two
Mixture.
Coupling agent is amino silicane coupling agent, epoxy silane coupling, isocyanates silane coupler or titanate esters
In class coupling agent any one or at least two mixture, wherein it is preferred that epoxy silane coupling；Additive is point
In powder, defoamer or levelling agent any one or at least two mixing, wherein, dispersant is modified polyurethane or acidity
In polyester and unsaturated polyamide and salt polymer；Defoamer is that modified alkanone, modified polyorganosiloxane or modified organic silicon gather
Compound；Levelling agent is polysiloxanes or acrylate copolymer.
The highly thermal-conductive resin composition also includes solvent, and solvent is acetone, butanone, methanol, alcohol, toluene, dimethylbenzene, N,
Any one in dinethylformamide, glycol monoethyl ether, propylene glycol monomethyl ether, ethyl acetate or cyclohexanone or at least two
Mixing.
A kind of high heat conduction metal-based copper-clad plate, including metal substrate and the above-mentioned high heat conduction tree coated in metallic substrate surfaces
Oil/fat composition；Described metal substrate is aluminium sheet, aluminium alloy plate, iron plate, ferroalloy plate or copper coin.The thickness selection of metal substrate
0.3-4.0mm.Metallic plate of the preferred surface of metal substrate by oil removing and roughening treatment.
The specific preparation process of high heat conduction metal-based copper-clad plate is as follows：
The first step：Weigh coupling agent be added in solvent be well mixed after it is standby；The solution prepared is used into spraying square
Formula is added in the mixed fillers of stirring, and 2h is handled in 110 DEG C of kneader；
Second step：Bi-maleimide modified epoxy resin, flexible modified epoxy are sequentially added, the first step is handled well
Heat filling, curing agent, curing accelerator 0.05-0.85 parts and additive；It is scattered at a high speed using 2000rpm/min
60min；At a high speed after scattered end, normal agitation curing 8h-12h, highly thermal-conductive resin composition is prepared；
3rd step：By the resin composition made in metallic substrate surfaces, at 160-190 DEG C, drying 2-6min makes
This resin composition system is in B-stage.Copper foil is sticked on aluminium sheet insulating barrier in B-stage, 170 in vacuum press
DEG C -200 DEG C, 10-35kg/cm2, after suppressing 90-200min, obtain metal-based copper-clad plate.
Embodiment 1~5 and comparative example 1~2
Each component and its content used in the composition epoxy resin of embodiment 1~5 and comparative example 1~2 are (by weight
Meter) as shown in table 1；Each component code name and its corresponding ingredient names are as follows：
(A) bi-maleimide modified epoxy resin：
(A1) N- is to the Maleimide-modified epoxy resin of carboxyl phenyl：It is N- to carboxyl phenyl maleimide and bis-phenol
It is prepared by the reaction of A types novolac epoxy resin；
(A2) diamine and bismaleimide compound modified epoxy：For diaminodiphenylsulfone, diphenyl ether span
Carry out acid imide and bisphenol A-type novolac epoxy resin copolyreaction is made；
(A3) dihydric phenol and bismaleimide compound modified epoxy：Come for pi-allyl bisphenol-A, diphenyl ether span
Acid imide and bisphenol A epoxide resin copolyreaction are made；
(B) flexible modified epoxy：
(B1) modifying epoxy resin by organosilicon, the production of SHIN-A companies of South Korea；
(B2) rubber modified epoxy resin：HyPox RA1340, the production of CVC companies of the U.S.；
(C) curing agent：Bisphenol A phenolic resin：SH-2107, Shandong Shengquan Chemical Industry Co., Ltd.'s production；
(D) heat filling：
(D1) breaking type aluminum oxide, AL-43-KT, Japanese Showa alumina producing；
(D2) breaking type aluminum oxide, AL-43-M, Japanese Showa alumina producing；
(D3) aluminium nitride, H05, the production of day Bender mountain company；
(E) curing agent accelerator：The ethyl imidazol(e) of 4- methyl -2, Japanese four countries' chemical conversion company production；
(F) coupling agent, epoxy silane coupling, Japanese chemical company of SHIN-ETSU HANTOTAI production；
(G) additive：
(G1) dispersant：BYK-9010, German BYK companies production；
(G2) defoamer：Perenol E7, BASF Corp. of Germany's production；
(H) solvent：Ethylene glycol monomethyl ether, DOW Chemical Co., Ltd.
The each component of high heat conduction metal-based copper-clad plate, embodiment 1~5 and comparative example 1~2 is prepared using above-mentioned preparation process
Content is as shown in table 1.
The embodiment 1~5 of table 1 and each component content of comparative example 1~2
The thermal conductivity of metal-based copper-clad plate made of testing example 1~5 and comparative example 1~2, peel strength, thermal stress,
The performance such as breakdown voltage, Hi-Pot, CTI, Tg, Td and pliability, its result is as shown in tables 2 and 3.
The performance test results of the embodiment 1~4 of table 2
The performance test results of the embodiment 5 of table 3 and comparative example 1~2
From table 2 and table 3 as can be seen that compared with prior art, the thickness that height of the present invention leads resin combination preparation is 100
Micron laminate dielectric layer has more than 1.8W/mK thermal conductivity and more than 6.0KV AC breakdown voltage.Also make Metal Substrate
Copper-clad plate insulating barrier has more excellent pliability, and with higher glass transition temperature and excellent heat resistance etc.
Performance.
Claims (10)
1. a kind of highly thermal-conductive resin composition, it is characterised in that by weight including following component：Bi-maleimide modified ring
Oxygen tree fat 40-75 parts, flexible modified epoxy 5-40 parts, heat filling 360-480 parts, curing agent 8-30 parts, coupling agent 2-6
Part, curing accelerator 0.05-0.85 parts, additive 1-5 parts.
2. highly thermal-conductive resin composition according to claim 1, it is characterised in that the bi-maleimide modified epoxy
Resin is N- to the Maleimide-modified epoxy resin of carboxyl phenyl, diamine and bismaleimide compound modified epoxy tree
Fat or dihydric phenol and bismaleimide compound modified epoxy any one or at least two mixing；
The N- is N- to the Maleimide-modified epoxy resin of carboxyl phenyl to carboxyl phenyl maleimide and epoxy resin
Reaction is made；
The diamine and bismaleimide compound modified epoxy are diamine, BMI and asphalt mixtures modified by epoxy resin
Fat ternary polymerization reaction gained, wherein diamine are MDA, diaminodiphenylsulfone, double (the 3- aminobenzene oxygen of 1,3-
Base) double (3- amino-benzene oxygens) phenylbenzenes of benzene or 4,4-；
The dihydric phenol and bismaleimide compound modified epoxy be dihydric phenol, bismaleimide compound and
Epoxy resin ternary polymerization reaction gained, wherein dihydric phenol are that diallyl bisphenol, diallyl Bisphenol F or diallyl are double
Phenol S.
3. highly thermal-conductive resin composition according to claim 2, it is characterised in that epoxy resin used in the modification is double
Phenol A epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, biphenyl type epoxy resin, alicyclic based epoxy resin,
Epoxy resins of phenol formaldehyde type, Study On O-cresol Epoxy Resin, bisphenol-A phenolic epoxy resin, dicyclopentadiene type epoxy novolac
In resin, aralkylphenol type epoxy resin, the polyfunctional epoxy resin of class containing naphthalene nucleus or anthracycline-containing polyfunctional epoxy resin
Any one or at least two mixing；Bismaleimide compound is to contain two or more maleimide in molecular structure
The compound of amine groups, it is diphenyl methane dimaleimide, Diphenyl Ether Bismaleimide or diphenyl sulphone (DPS) bismaleimide
Amine.
4. highly thermal-conductive resin composition according to claim 1, it is characterised in that the epoxy resin of the flexible modification is
Modifying epoxy resin by organosilicon, acrylonitrile butadiene rubber modified epoxy resin, dimer acid modified epoxy resin or soybean oil modified asphalt mixtures modified by epoxy resin
In fat any one or at least two combination.
5. highly thermal-conductive resin composition according to claim 1, it is characterised in that the curing agent is phenol Linear phenol
Urea formaldehyde, ortho-cresol novolac resin, bisphenol A phenolic resin, dicyclopentadiene type phenolic resin, phenolic resin containing naphthalene nucleus, aralkyl
Base phenol type phenolic resin, two amine type benzoxazines, bisphenol A-type benzoxazine, bisphenol-f type benzoxazine or modified by cardanol benzene
In Bing oxazines any one or at least two combination.
6. highly thermal-conductive resin composition according to claim 1, it is characterised in that the heat filling is electrical conductivity 50
Below μ s/cm breaking type aluminum oxide, spherical type aluminum oxide, alumina whisker, aluminium nitride, boron nitride, magnesia or carborundum
In any one or at least two mixing.
7. highly thermal-conductive resin composition according to claim 1, it is characterised in that the curing accelerator is imidazoles
Compound, wherein, glyoxaline compound is 2-methylimidazole, 2-ethyl-4-methylimidazole, 2- phenylimidazoles, 2- undecyl miaows
Azoles, 1 benzyl 2 methyl imidazole, 2- heptadecyl imidazoles, 2 isopropyl imidazole, 2- phenyl -4-methylimidazole, 2- dodecyls
In imidazoles or 1- 1-cyanoethyl-2-methylimidazoles any one or at least two mixture.
8. highly thermal-conductive resin composition according to claim 1, it is characterised in that described coupling agent is that amino silane is even
Join in agent, epoxy silane coupling, isocyanates silane coupler or titante coupling agent any one or extremely
Few two kinds mixture；Additive is the mixing of any one or at least two in dispersant, defoamer or levelling agent, its
In, dispersant is in modified polyurethane or acidic polyester and unsaturated polyamide and salt polymer；Defoamer is modified alkane
Ketone, modified polyorganosiloxane or silicon modified organic polymer；Levelling agent is polysiloxanes or acrylate copolymer.
9. highly thermal-conductive resin composition according to claim 1, it is characterised in that the highly thermal-conductive resin composition also wraps
Solvent is included, solvent is acetone, butanone, methanol, alcohol, toluene, dimethylbenzene, DMF, glycol monoethyl ether, third
In glycol methyl ether, ethyl acetate or cyclohexanone any one or at least two mixing.
A kind of 10. high heat conduction metal-based copper-clad plate, it is characterised in that including metal substrate and coated in metallic substrate surfaces as
Highly thermal-conductive resin composition described in claim any one of 1-9；Described metal substrate is aluminium sheet, aluminium alloy plate, iron plate, iron
Alloy sheets or copper coin.
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| CN107011657B (en) * | 2017-03-28 | 2019-05-21 | 中国科学院化学研究所 | A kind of high-ductility bimaleimide resin and its preparation method and application |
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